Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine

被引:92
作者
Guzel, Emre [1 ]
Atsay, Armagan [1 ]
Nalbantoglu, Sevgi [2 ]
Saki, Neslihan [2 ]
Dogan, A. Lale [3 ]
Gul, Ahmet [1 ]
Kocak, Makbule Burkut [1 ]
机构
[1] Istanbul Tech Univ, Dept Chem, TR-34469 Istanbul, Turkey
[2] Kocaeli Univ, Dept Chem, TR-41380 Kocaeli, Izmit, Turkey
[3] Hacettepe Univ, Inst Canc, Dept Basic Oncol, TR-06100 Ankara, Turkey
关键词
Phthalocyanine; Hexadeca-substituted; Amphiphilic; Microwave irradiation; Photosensitizing activity; In-vitro; WATER-SOLUBLE PHTHALOCYANINES; EFFICIENT PHOTOSENSITIZERS; METAL-FREE; THERAPY; PHOTOPHYSICS; AGGREGATION;
D O I
10.1016/j.dyepig.2012.12.027
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new phthalonitrile derivative bearing hexyloxy groups in the 3,6- positions and p-sulfonylphenoxy-and chloro groups in the 4 and 5- positions was synthesized. The new hexadeca-substituted zinc phthalocyanine was obtained by cyclotetramerisation of this phthalonitrile derivative in the presence of anhydrous zinc acetate under microwave heating. The aggregation behavior of the amphiphilic zinc phthalocyanine was studied in methanol and water. All novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, H-1 NMR and MS spectroscopic data. The photosensitizing activity of this phthalocyanine dye was evaluated by application of 1,3-diphenylisobenzofuran as a singlet oxygen chemical quencher. In cell culture media the phthalocyanine showed a cytotoxic effect on HepG2 cells; a feature which encourages future in vivo studies. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:238 / 243
页数:6
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